The Naughty Assistant: A Novel of Erotic Punishment by Imelda Stark

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The Naughty Assistant: A Novel of Erotic Punishment

(Imelda Stark)


THE NAUGHTY ASSISTANT:

About the Author

 

Imelda Stark is the nom de plume of a teacher and practitioner of psychotherapy at a major East Coast medical school (hence the need for a pseudonym). She has been exploring the psychologically complex realm of BD/SM for twenty-four novels now. Imelda strives to combine the eroticism she feels around challenging things happening to willing bottoms with an exploration of how we aficionados of these painful pleasures got to be the way we are. She welcomes and will respond to email at imeldastark1@gmail.com.


Chapter One

 

Alyssa Addams always wanted to be a good girl. From the bottom of her heart. From her earliest memories she longed to please her parents, teachers, Scout leaders and coaches, girlfriends, and boyfriends. This often led to unhappy complications, especially as she grew older. Too many times to count, doing what would please the person in front of her ended up making someone else (like a parent, teacher, or police officer) disappointed or even downright angry. And in the tight-knit working class community where she grew up, this kind of situation tended to be resolved in one simple, old-fashioned way. That would be with her skirt raised and panties lowered and way too much painful attention being paid to her poor quivering buttocks.

Whether it was at home or at school, it just seemed that some wicked imp inside our Alyssa would routinely subvert her best intentions to do as she was told. No matter how hard she tried, though, her attention would wander or some fascinating distraction would present itself and away her focus would go on to the new shiny object that caught her gaze. It seemed that dawdling was her default modus operandi. And when your Dad is a policeman always working double shifts and your Mom is a busy hairdresser with appointments to keep with demanding clients, there is precious little leeway to accommodate a child who chronically keeps everyone waiting. So all too many days began with our heroine wiping away her sniffles as she sat on a very tender bottom in class or Mass or Sunday school. And of course, the wiggles caused by that very discomfort could end up with a second embarrassing trip over a teacher's or nun's knee. Though at least these extramural spankings tended to be through her panties rather than on her poor bare heinie.

But all of these trials and tribulations never served to quench Alyssa's sweet temperament or her genuine desire to please all of the adults who seemed to get so upset with her. She took her punishments bravely and without complaint, since clearly they were justified by her wayward mind. Stern Sister Agatha in fourth grade once remarked as her massive wooden ruler was colliding all too enthusiastically with our protagonist's chubby backside: 'There's a devil in you, girl, and we are all going to beat it out of this naughty rear end whether you like it or not!' The pretty blonde blue-eyed child could hardly argue with that logic, even though her poor bottom cheeks would have disagreed quite fiercely if they had been asked.

By that point, the cute protagonist of this story had in fact actually started to like her almost daily trips over one frustrated grownup's lap or another's, though she would never have admitted it even to herself. Alyssa loved attention, and neither of her parents was of a mind to spare much of that apparently precious commodity for their only offspring. Kids are funny that way, especially those born with a strongly affiliative nature like the star of this tale. And if they don't get it by being charming (which she worked very hard to be) and being naughty works, then naughty they will be. And if it takes earning a bare bottomed trip over an angry adult's lap to get to be the center of a desirable grownup's attention, children like her will arrange to have that happen as often as they need.

It was just about this age, when Alyssa's breasts had started to seriously declare themselves and her hips had likewise begun to broaden toward their eventual blatantly feminine proportions that an additional twist emerged to her already complicated life. Many of the boys, and certain of the girls, at her parochial school seemed to take special notice of the previously invisible heroine of our tale. And certain of the naughtier ones of each gender, who also seemed to take a disproportionate amount of disciplinary attention to their own bottoms from the nuns, began to seek out our darling Alyssa for private trysts.

The prematurely buxom girl was only too happy and pleasantly surprised to be noticed by boys and girls who previously had occupied a social circle unreachably above her and her fellow misfit friends. That these whispered meetings took place in private and seemed to invariably involve being touched on her embarrassingly large breasts and having her already lightly furred pussy felt up was a bit unnerving to the innocent girl. But she was so anxious to please these amazing new friends that she gladly submitted to whatever they wanted to do to her. And the truth was, she not only liked the attention but also really, really liked the way it felt when either a boy or girl touched her titties (especially the nipples) and all of the very sensitive places between her legs.

And if she enjoyed receiving such attentions, far be it from our heroine (who always was a person of great generosity of spirit) to withhold similar pleasures from those who chose her for this special honor. So Alyssa learned just how boys liked to have their hungry cocks stroked and fondled. Soon she was shocked to see that if she did it long enough there was a sudden eruption of a fluid that seemed a lot like snot, but smelled very differently. And the girls who sought her out seemed to have their own version of a very happy paroxysm in their bodies when she stroked the little button at the top of their slits just right. But most wonderful of all, one of the naughtiest girls did that very thing to her own pussy and our heroine experienced the first of a lifetime of delightful explosions. She had never known anything like the waves of electric pleasure that shot through her whole body like the lightning in Frankenstein's monster, only a whole lot more enjoyable than it seemed to him.

That very night, she was taken over her stern Mommy's knee for being home an unprecedented whole hour late because of the games she and the naughty girl were playing in their special fort inside an overgrown bramble bush. Alyssa felt very sad about what was going to happen to her poor heinie, since this was the latest she had ever been because she and her nice new friend had so many things to do to each other. Mommy had gotten out the hairbrush, and her face was beet red as she raised her weeping daughter's pleated plaid uniform skirt and dragged down her white cotton panties with more energy than usual. And it seemed that the older woman had some awareness that something uniquely punishable had been going on, because she delivered the most blistering spanking that Alyssa had ever experienced.

The pain was unimaginable, but as the penitent sobbing girl became more frantic, a feeling between her legs a lot like the one she had just experienced an hour earlier began to grow. And before the spanking ended, our heroine experienced an even more powerful version of the same explosion that her friend had introduced to her, right there on Mommy's lap as her poor heinie was getting mercilessly blistered. The ritual at home was that spanked girls were allowed to take a bath after doing their corner time with their throbbing buttocks on display while they thought about their sins. And as soon as the still-sniffling girl lowered her poor inflamed rear end into the warm water, she reached for that same spot on her own pussy for the first time. Within seconds, yet another wonderful electrical phenomenon erupted through her entire body, and a lifetime career as a committed masturbator was born.


Chapter Two

 

Over the next few years, our heroine's circumstances evolved in several interesting but increasingly challenging directions. First of all, the kinds of things she was doing with her new circle of nice boyfriends and girlfriends began to change. The same girl who had done Alyssa the wonderful favor of introducing her to her orgasm (she looked up the word in a dictionary at the public library, since the parochial school would never have permitted such things in the school library) had all sorts of other fascinating ideas for private naughty fun. Soon the buxom young woman discovered how good it felt to have her adventurous friend suck on her breasts and nipples while playing with her clitoris (yes, she looked that up too). This gave her wonderfully intense orgasms, which she was only too glad to give back to her thoughtful classmate.

And even better, one time on a sleepover when her friend's parents had passed out from their nightly drinking bout, a delightful new activity was introduced. It seemed that some girls liked kissing and licking between other girls' legs, and Alyssa's friend was one of them. And when she did this, which seemed kind of dirty even to our naughty girl, a new level of wonderfulness happened when she had her beloved explosion. Of course, she was only too happy to return the favor to her generous friend, whose pussy was easier to eat (she suspected) since it didn't have any yucky hairs on it like her own.

By this point, Alyssa's Daddy had stopped spanking his daughter, muttering that even though she was just as naughty as ever, she was getting too big to go over his lap. This made her sad, since her trip across his knee were the only times he ever held or touched her, and she had better orgasms during his punishments of her than when her mean Mommy spanked her. But Mommy seemed to make up for having to take on the chore of punishing her chronically wayward daughter by always using the hairbrush on the star of our story, and spanking her so hard that try as she might she couldn't hold still. This meant that the frustrated older woman would have to capture her daughter's frantically kicking legs between her panty-hosed thighs, and use her left hand to hold Alyssa's left wrist. That hand had a mind of its own and always seemed to try to protect her poor buttocks, no matter how many times it failed, so it needed to be secured at the small of her back. This bent the penitent girl much more sharply over her Mommy's left thigh. And even worse, it showed her now-fully-blonde-fledged pussy quite blatantly, which embarrassed her so much she thought she would die from blushing. And indeed, her face got just as red as her sizzling bottom cheeks.

But yet again, something weird and unexpected happened. There must have been a part of Alyssa that got turned on by being embarrassed in much the same way as she was aroused by being spanked. For the more humiliated she was by knowing that her mad Mommy could see her naked furry blonde pussy (and how wet and swollen it was from how sexually excited its owner was), and the more severe her backside pain, the harder our heroine's climax. The final time, when she already had the body of a grown woman, her orgasm was so violent and earth-shattering that she bucked her way off her appalled Mother's lap. The older woman muttered: 'There's something wrong with that girl...' as she stormed off in a confused dither. But that incident tolled the final bell on Alyssa's domestic disciplinary experiences. From that day neither of her parents laid a punishing finger on her no matter how naughty she was.

And to be sure, our ever-well-intended heroine continued to have the very same problems with unconsciously defying authority that she always had. In fact, as she became more sexually active, they got even worse. For in parallel to the wicked girl Emily who had introduced the star of our story to lesbian sex, a very bad boy in her class made a similar discovery about the buxom blonde youngster. Brad was very handsome in a skater-boy way, and shared Emily's home circumstance of neglectful parents (though his were addicted to the marijuana they dealt on the side to support their nominal careers as artists). Soon he had persuaded Alyssa to suck his cock until he came in her mouth. Even though this was pretty yucky, he seemed to enjoy it so much that the anxious-to-please girl was happy to go down on her knees and repeat the performance any time he asked and they could find a private place. He also taught her to play gently with his balls while she sucked him, which seemed to give him even better orgasms and make him like her even more.

Unlike Emily, who seemed to enjoy giving sexual pleasure as much as receiving it, Brad seemed quite content to take without returning the favor. Even though she kind if guessed that boys tended to be self-centered in this way, it hurt Alyssa's feelings that he never paid attention to her pleasure. But she still liked him a lot and always got very turned on whenever they played their private games. Then she would be left to relieve her own tension with her trusty right hand once they had parted. She would think about how interesting his penis was, and what it would feel like inside her pussy (which seemed to want it pretty badly), and sometimes even if he might take her over his lap like her Daddy used to and spank her bottom until she came really hard. This last fantasy always got her off the best, so she saved it up for when she was feeling particularly lonely and in need of extra soothing.

But Brad surprised her one day when they were alone at his parent's messy apartment where they often went for her to suck him off when his Mom and Dad were on a 'buying trip' to a pot farm in Mendocino. She knelt as usual to unzip him, when he pulled out a funny flat foil package that she didn't recognize. Their school didn't believe in sex education, since the Pope said that no one was to have that kind of fun until they were married, and then only to make babies. Her way-too-cute boyfriend said it was a condom, and that it would keep them both safe while they had real sex.

This was scary but even more exciting for Alyssa. She gladly helped him unroll the funny rubber thingy inside the foil to completely cover his cock. And she was even more happy to take off all her clothes and lay down on his parents' bed, which smelled of pot smoke and grown-up sex. He actually kissed her then, which he hadn't done for months, preferring her mouth to be engaged in other activities that he seemed to find more useful for his purposes. Even better, he even kissed her titties, though not nearly so nicely as Emily. In fact, he was kind of rough with them, sucking hard and first nibbling and then really biting her nipples. As that jolt of pain sent a signal straight between her legs shocked them both by having an orgasm right there, without him even touching her pussy, let alone being inside it. Once she had calmed down Alyssa kind of wondered if there was anything painful or degrading that wouldn't turn her on. But she was nonetheless grateful that he had finally given her some real pleasure. And she liked it even more when he stripped off his clothes to be nude with her for the first time.

But this preliminary nipple-stimulated climax was the mildest of preludes to what followed next. Brad joked a bit uncomfortably: 'Damn, Lyss, you are one scary hot chick...are you ready to be fucked for real?' Our heroine was both turned on and a bit shocked at hearing what they were about to do being named so frankly. But there was not the slightest doubt in her mind (and especially in the part of her on the verge of experiencing its intended biological purpose for the first time) that she wanted his cock inside her, and the sooner the better. She looked up at him, her face flushed with erotic excitement, and nodded a sincere yes. Her innocent cornflower-blue eyes glowed with unabashed adoration of her wonderful boyfriend who was about to relieve her of her virginity.

Brad indeed looked angelic (in a bad-boy sort of way) in the dim light of his parents' dingy bedroom. His long dark hair was flowing around his handsome face and his lean olive skinned body made a stark contrast to her blonde fleshy nakedness. Alyssa moaned as he took his latex sheathed erection in his right hand while he held himself suspended above her on his knees and left arm. He guided his cock clumsily against her pussy, which was already suffused with blood and glistening with the evidence of its hearty welcome for its new best friend. She wiggled a bit to ease it inside, sighing at the pleasure of it as her introitus was stretched for the very first time ever.

But then everything seemed to hit a road block. There was apparently some part of her body that kept him from going more than an inch inside her. Alyssa's mother didn't approve of tampons, so for the years she had been having periods she had always used so-called 'sanitary napkins' (which hardly seemed sanitary when she flushed their blood-soaked remains down the toilet). So she had never tried to put anything 'up there', and the hymen she had read about in her furtive public library researches on matters erotic was not just a theoretical impedance to Brad's plans.

Alyssa told him it was hurting her, but he seemed so forlorn when she asked him to wait, and she just hated to disappoint him. So she said to go ahead and not worry about her, which raised his spirits immediately. His muscular skater-boy hips surged, and our heroine felt a shocking pain inside her pussy as something seemed to tear, and he pushed inside her, every inch hurting as bad as the hardest spanking she'd ever gotten. She started to cry, but then as usual when anything excruciating happened to an erotic part of her body, she felt a flood of arousal as his pubic bone jammed against her clitoris.

Brad was too wrapped up in his own experience of fucking her (which, though he hadn't told her, was his first time as well) to notice Alyssa's distress, and he began fervently fucking away. This turned out to be just fine for her, since the combination of the pain of her deflowering with the pleasure of his cock inside her and his body pressing hard into her clitty on every thrust made her start coming very hard. And unlike the other times when she had climaxed, it seemed that being fucked meant that her orgasms piled one on top of the other. Perhaps four of them happened in the next ten minutes while Brad happily pumped away inside her, and then he yelled really loud and got red and made an even more funny face than when she gave him a hand job or blow job. Alyssa could feel his cock pumping inside her almost as completely as she could when he came in her mouth, but this was so much better since she didn't have to deal with his yucky come. When he finally collapsed on top of her, they were both sweaty and breathing hard, and he said he loved her and would always be her boyfriend, and she was the happiest she had ever been in her life.